I will try to plot a course between the twin reefs of “analysis paralysis and sunk cost fallacy”. I’ll take your advice on getting something that works for the moment and improving on anniversaries, at my age every day is an anniversary of something or other
Hey Marcus1! I'm not going to recommend any particular eyepiece for you but will say don't be afraid of the used market. You can try various eyepieces (and/or telescopes, filters, etc.) and if they are disagreeable to you they can be sold for the same amount you paid for them usually. All you'd be out is some shipping expenses to get some hands on experience.
Also +1 on a chair. Sitting to observe adds about 25% to the size of any scope! Enjoy the journey.